Hydrochloric Acid → HCID 67314789, compound

HRID 1011353Notes

Reaction equation

HRID 1011353 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:22][O:23][CH:24]=[CH:25][C:26]1[N:31]=[C:30]2[CH2:32][O:33][C:34](=O)[C:29]2=[CH:28][CH:27]=1.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:34]1[C:29]2[C:30](=[N:31][C:26]([CH:25]=[CH:24][O:23][CH3:22])=[CH:27][CH:28]=2)[CH2:32][O:33]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 67313859HCID 67313859, compound

Product 1

HCID 67314789HCID 67314789, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 5-fluoro-1,3-dihydro-indol-2-one (176 mg, 1.16 mmol) in THF (5 mL) is treated with a solution of lithium bis(trimethylsilyl)amide (2.3 mL of a 1 M solution in THF, 2.3 mmol) dropwise. The resulting solution is stirred at room temperature for 10 min. A solution of 2-(2-methoxy-vinyl)-7H-furo[3,4-b]pyridin-5-one (111 mg, 0.58 mmol) in THF (2 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 3 h and is poured into cold 10% aqueous HCl solution (30 mL) at 0° C. The resulting mixture is stirred at 50° C. for 1 h and room temperature overnight. The solid which formed is collected by filtration and dried to give the title compound as a light brown solid (65 mg, 35%).

Workup

  1. stirringThe resulting solution is stirred for 3 h
  2. stirringThe resulting mixture is stirred at 50° C. for 1 h and room temperature overnight
  3. customThe solid which formed
  4. filtrationis collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-b0ff5b09834c48f989cb6bda48252bf7
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

Loading…